Cellulosic textile finish with 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone, zinc nitrate and a sequestering agent

ABSTRACT

A finish for cellulosic textile materials to give a wrinkle resistant and permanent crease to said textile materials, wherein the finish contains a sequestering agent making it compatible with other operations performed on the textile.

United States Patent 1191 1111 3,890,095 Bann et a1. June 17, 1975 [54] CELLULOSIC TEXTILE FINISH WITH 3,029,164 4/1962 Seki l17/139.4 3 0 4 5 x 2 3,183,195 5/1965 Hushebeck 252/428 A Husllebeck SEQUESTERING AGENT 3,216,780 11/1965 Landells 8/1 16.3

Inventors: Robert Francis Bann, Somerville;

William Joseph Moran, Martinsville; Philip B. Roth, Somerville, all of NJ.

American Cyanamid Company, Stamford, Conn.

Filed: Apr. 23, 1973 Appl. No.: 352,778

Related U.S. Application Data Continuation-impart of Ser. No. 114,380, Feb. 10, 1971, Pat. No. 3,746,505, which is a continuation of Ser. No. 672,450, Oct. 3, 1967, abandoned, which is a continuation-in-part of Ser. No. 628,573, April 5, 1967, abandoned.

Assignee:

U.S. Cl. 8/185; 260/29.4 R Int. Cl.. D06p 5/02; D06m 13/12; D06m 13/34 Field of Search 8/116 R, 185, 181

References Cited UNITED STATES PATENTS 1/1956 Reibnitz 117/64 3/1961 Mann 117/1l9.8

FOREIGN PATENTS OR APPLICATIONS 919,635 2/1963 United Kingdom 936,993 9/1963 United Kingdom OTHER PUBLICATIONS Primary Examiner-Leland A. Sebastian Assistant Examiner-Donald P. Walsh Attorney, Agent, or FirmRobert P. Raymond ABSTRACT A finish for cellulosic textile materials to give a wrinkle resistant and permanent crease to said textile materials, wherein the finish contains a sequestering agent making it compatible with other operations performed on the textile.

11 Claims, No Drawings CELLULOSIC TEXTILE FINISH WITH 1,3-DIMETHYLOL-4,5-DIHYDROXY-2- IMIDAZOLIDINONE, ZINC NITRATE AND A SEQUESTERING AGENT This application is a continuation-in-part of application Ser. No. 114,380, filed Feb. 10, 1971 now U.S. Pat. No. 3,746,505, which in turn is a continuation of application Ser. No. 672,450, filed Oct. 3, 1967, now abandoned, which was a continuation-in-part of application Ser. No, 628,573, filed Apr. 5, 1967, now abandoned.

This invention relates to a nondiscoloring, durable press finish for dyed or undyed, cellulosic textile materials, More particularly, it relates to a process of applying an aqueous finish containing l,3-dimethylol-4,5- dihydroxy-2-imida2olidinone of Formula I, a Zinc nitrate catalyst and a sequestering agent to cellulosic materials, and to the treated cellulosic materials.

l,3-Dimethylol-4,5-dihydroxy-2-imidazolidinone is a very valuable finishing agent for textile materials. It has a wide and extensive use on cellulosic materials and blends of cellulosic materials with other fibers such as polyamides (nylon) and polyesters (Dacron). It is generally used together with sodium acetate. Although it can be used as a conventional wash-and-wear finish, its greatest use is in the durable press field, especially in the postcure process as described in U.S. Pat. No. 2,974,432. Zinc nitrate is the preferred curing catalyst. The finish has not, however, been entirely satisfactory since it is not compatible with other operations performed on the textile materials. For example, it has been found that it causes scorching on white goods during the pressing operation and yellowing during the postcuring operation.

Moreover, it has not been found to be satisfactory for use with certain resin sensitive dyes such as a group of blue vat dyes based on indanthrone (Formula ll) and its chlorinated derivatives thereof which have considerable commercial value.

When a cellulosic fabric dyed with one of the indanthrone dyes is treated with a textile finish containing l,3-dimethylol-4,5-dihydroxy-Z-imidazolidinone, followed by a curing operation in the presence of zinc nitrate as the curing catalyst, the shade of the fabric is severly altered, becoming duller and much greener. The color change is so drastic that cloth dyed with one of the indanthrone dyes cannot, therefore, be treated with a wrinkle resistant finish containing 1,3- dimethylol-4,5-dihydroxy-Z-imidazolidinone and Zinc nitrate.

Zinc nitrate is the preferred catalyst for use in curing l,3-dimethylol-4,5-dihydroxy-Z-imidazolidinone. Other zinc salts, such as zinc chloride and zinc sulfate, do not produce the desired wash-and-wear" properties. Other curing catalysts, such as magnesium chloride, are also not as satisfactory as zinc nitrate and are not used.

Therefore, the need exists for a method of applying and heat curing a textile finish containing [3 dimethylol-4,5-dihydroxy-2-imidazolidinone with the Zinc nitrate catalyst to give a wrinkle resistant or permanent crease finish which is compatible with other.

operations, particularly with white cellulosic materials which will prevent or reduce l) yellowing on curing. and (2) scorching on hot pressing, and with cellulosic materials dyed with resin-se,nsitive" dyes.

It is therefore an object of this invention to provide a finish and a method for rendering cellulosic textile materials wrinkle resistant or providing a permanent crease, said finish being compatible with other opera' tions on said textile material.

A further object is to provide a method and finish for undyed cellulosic textile materials incorporating 1,3- dimethylol-4,5-dihydroxy-Z-imidazolidinone and zinc nitrate, for obtaining wrinkle resistance or permanent creases on said textiles, which does not cause yellowing on curing or scorching on hot pressing or ironing after washing.

Another object is to provide a method and finish for cellulosic textile materials incorporating 1,3- dimethylol-4,5-dihydroxy-2-imidazolidinone and zinc nitrate, for obtaining wrinkle resistance or permanent creases on said textiles, which does not discolor, resin sensitive" dyes on said textile materialsv A further object is to obtain an undyed textile material which is wrinkle resistant or permanently pressed and which does not yellow on curing or scroch on pressing.

Another object is to obtain a dyed textile material which is wrinkle resistant or permanently pressed and wherein the shade is not discolored.

These and other objects of the invention will become apparent as the description thereof proceeds.

A method has now been discovered for applying 1,3- dimethylol-4,5-dihydroxy-2-imidazolidinone to undyed cellulosic materials which will prevent or reduce yellowing on curing and scorching on hot pressing and to dyed textile materials to prevent discoloration of the dye.

In the process of the invention an aqueous solution of l,3-dimethylol-4,5-dihydroxy-2-imidazolidinone, a sequestering agent, and zinc nitrate is applied to the cellulosic textile material. The textile material is then dried and the finish is cured at an elevated temperature. in a postcure process, the dried fabric is made into a garment or other article which is then pressed and cured.

Cellulosic textile material has the usual meaning and includes blends with other fibers such as polyamides (nylon) and polyesters (Dacron), including woven, knitted, felted, or other textile goods, for example.

Suitable sequestering agents for use in this invention are described in Volume 12, page 164, of Enyclopedia of Chemical Technology, first edition, and in Organic Sequestering Agents by Chaberek 1959).

The two principal classes of sequestering agents which are suitable are the aminopolycarboxylic acids, such as ethylenediaminetetraacetic acid, nitrilotriacetic acid, di(hydroxyethyl)glycine, (hydroxyethyl)ethylenediaminetriacetic acid and diethylenetriaminepentaacetic acid, and the hydroxycarboxylic acids, such as gluconic acid, citric acid, malic acid and tartaric acid. These are used as partially neutralized alkali metal salts.

The resin sensitive dyes include certain dyes of several classes, such as direct dyes, sulfur dyes, reactive dyes, disperse dyes, vat dyes, and particularly indanthrone vat dyes.

The indanthrone dyes include indanthrone (C.l. Vat Blue 4, C. I. No. 69800), dichloroindanthrone (C.l. Vat Blue 6, C.l. No. 69825), monochloroindanthrone (C. l. Vat Blue 14, C. l. No.-698l), mixture of mono-, diand trichloroindanthrone's(C. l. Vat Blue 10, C. 1. No. 69830), etc.

The sequestering agent can be put on the cellulosicmaterials simultaneously with, prior to or subsequent to the application of the 1,3-dimethylol-4,5-dihydroxy-Z-imidazolidinone and zinc nitrate. It is preferred to apply the imidazolidinone, zinc nitrate and sequestering agent from the same aqueous solution. However, the sequestering agent can be applied from an aqueous solution before or after the application of the imidazolidinone and zinc nitrate.

The aqueous solution of l,3-dimethylol-4,5-dihydroxy-2-imidazolidinone, sequestering agent, and zinc nitrate is applied to the textile material by any of the normal methods of application, such as by padding, spraying, dipping and the like.

The amount of l,3-dimethylol-4,5-dihydroxy-2- imidazolidinone applied to the textile materials should be between 1.0 and 25.0 percent, preferably between 3.0 and 8.0 percent, based on the weight of the textile material.

The amount of sequestering agent used should be between 0.05 and 3.0 percent, preferably between 0.15 and 1.0 percent based on the weight of the solution. This corresponds to between about 0.025 and 3.0 percent, preferably between about 0.075 and 1.0 percent. based on the weight of the fabric.

The amount of zinc nitrate should be between 5.5 and 16.5 percent, preferably between 9.5 and 12.5 percent, based on the weight of the imidazolidinone.

The treated fabric may be dried and cured by conventional wash-and-wear procedures. Also, the well known postcuring procedure of US. Pat. No. 2,974,432 can be used. which consists of drying the treated fabric; cutting, sewing and pressing the garment; and curing the finish on the garment at an elevated temperature.

The treated textile material is normally dried before the pressing and curing operations are performed. A drying temperature between 175 and 250F.. preferably between 200 and 22-5F., is used. The pressing operation can be done by any of the methods well known in the trade, such as by the use of a hot head press. The pressing operation is carried out at'a temperature of 300 to 420F. In the curing operation, the pressed fabric is heated at an elevated temperature under conditions normally used by the trade which is at a temperature between 300 and 420F., preferably between 320 and 380F., for a period sufficient to react the imidazolidinone with the cellulosic fabric. Heating periods between 5 and 20 minutes are normal.

The textile finish of this invention is compatible with many fluorescent brightening agents normally used on cellulosic materials, particularly the stilbene class of brightening agents.

Undyed cellulosic fabrics treated by the process of this invention have good resistance to scorching and discoloration when the fabrics are pressed and cured at elevated temperatures.

In one preferred embodiment of the invention with dyed fabrics, a cotton fabric dyed with an indanthrone vat dye is padded with an aqueous solution containing about 9 percent of l,3-dimethylol-4,5-dihydroxyimidazolidinone, about 1 percent of zinc nitrate and about 0.35 percent of ethylenediaminetetraacetic acid, tetrasodium salt. The treated fabric, containing about 6 percent of the imidazolidinone is dried at 225F. The dried fabric is then cut and sewed into garments which are pressed at about 310F. The pressed garments are then heated in an oven at about 340F. until the imidazolidinone is cured on the garment. The thus treated garment is durably pressed" where creases are desired and is wrinkle resistant in those areas where wrinkles and creases are not desired. During the pressing and drying operation the shade of the dyed fabric is essentially unchanged.

It has been discovered thatthe sodium acetate normally used in the finish containing 1,3-dimethylol-4,5- dihydroxy-2-imidazolidinone to decrease the initial losses in tensile strength, tear strength and'abrasion resistance is not required when the sequestering agent is used. Additionally, the sequestering agent appears to give more stable pad baths than sodium acetate. It has been found that the sequestering agent used in the invention does not cause precipitation of thefluorescent brightening agents in finishing baths.

The nonionic surface active agent used in the examples is the condensation product of nonylphenol with an average of 9.5 moles of ethylene oxide. Other suitable nonionic surfactants can also be used, such as other alkyl aryl polyethylene glycol ethers and ethylene oxide adducts of straight chain alcohols.

The fluorescent brightening agent used on undyed goods is C. l. Fluorescent Brightening Agent 25, a compatible brightening agent. It is a commercial product belonging to the sulfonated diaminostilbene class of brightening agents and was employed as an aqueous solution. In addition to this particular brightening agent, any other suitable ones can be used such as other members of the sulfonated diaminostilbene class, providing they are compatible with the other components of the finish.

For commercial application, it is often desirable to prepare a resin mix containing the imidazolidinone, sequestering agent and water to which the zinc nitrate, preferably as an aqueous solution, is added to form the pad baths prior to use. Suitable resin mixes contain between 1 and 90 percent imidazolidinone, a preferred range beingbetween 30 and 50 percent; between 0.1 and percent sequestering agent, a preferred range being between 1.0 and 4.0 percent.

Pad bath preparation is greatly simplified by controlling the extent of neutralization of the sequestering agent in such a manner that when the zinc nitrate catalyst has been added, a pad bath having the sequestering agent in the desired degree of partial neutralization is produced without the need for further addition of acid or base.

The following specific examples are set forth to illustratethe preset invention and are notintended to be limitative thereof. Parts and percentages. used herein are by weight unless otherwise indicated.

EXAMPLE 1 Eightaqueous pad baths were prepared, each bath containing 11.2 percent of 1,3-dimethylol-4,5-dihydroxy-2-im'idaz'olidinone, 1.25 percent of zinc nitrate, 0.25 percent of a nonionic surface active agent. 0.5

percent of C. I. Fluorescent Brightening Agent 25, and

sodium acetate or a sequestering agent as shown in Table I. The pH of the pad baths was adjusted to 4.7 by addition of sodium hydroxide or hydrochloric acid as required.

(hydroxyethyl )ethylenediaminetriacetic acid, trisodium salt The pad baths were applied by standard padding procedure to a 65/35 polyester/cotton fabric obtaining a .70 percent wet pickup. The fabrics, containing 7.9 percent on the weight of the fabric of l,3-dimethylol-4,5-

dihydroxy-Z-imidazolidinone, were dried for 1 minute at 225F., steamed for 5 seconds, pressed for 5 seconds at 350F., and heated in an oven at 320F. for 8 minutes. I

The fabrics were examined for discoloration by comparing the color of the treated fabrics with that of the untreated fabric.

The fabrics were laundered 5 times in a homestyle washing machine using water at 130 140F. and a detergent followed by a rinse water treatment at about I10-120F. and tumble drying after each washing. The

fabrics were theninspected for retention of creases placed in the fabric during the pressing operation.

The results are shown in Table II. Fabrics A-H correspond to pad baths A-H, respectively.

TABLE II Fabric Discoloration Crease Retention A Severe Excellent B Severe C Very slight D Slight TABLE II-Continued Fabric Discoloration Crease Retention E Slight F Very slight G Slight H Slight The above results demonstrate the effectiveness of various sequestering agents in reducing the discoloration of polyester/cotton fabrics when treated with 1,3- dimethylol-4,5-dihydroxy-2-imidazolidinone and zinc nitrate.

EXAMPLE 2 TABLE III Pad Bath Additive A 00771 sodium acetate B 0.3% ethylenediaminetetraacetic acid.

I tetrasodium salt C 0.37: diethylenetriaminepentaacetic acid. pentasodium salt D 0.3% N,N-di(hydroxyethyl)glycine, sodium salt E 0.3% (hydroxyethyl )ethylenediaminetriacetic acid. trisodium salt The pad baths were applied by standard padding procedure to cotton broadcloth obtaining a 73 percent wet pickup. The fabrics, containing 5.8 percent on the weight of the fabric of l,3-dimethylol-4,S-dihydroxy-Z- imidazolidinone, were dried at 225F. for 1 minute. Swatches of the dried fabrics were cured for 1 minute at 360F.

The wrinkle recovery of the cured fabrics was measured by tentative test method 66 1959 T of the American Association of Textile Chemists and Colorists.

The results are shown in Table IV. Fabrics A-E correspond to pad baths A-E, respectively.

TABLE IV Fabric Wrinkle Recovery, W & F. degrees A 275 B 261 C 261 D 281 E 260 Untreated 227 These results show the lack of adverse effect of the sequestering agents on the wrinkle recovery properties of a cotton fabric treated with a finish containing 1,3- dimethylol 4,5-dihydroxy-2-imidazolidinone.

EXAMPLE 3 Six aqueous pad baths were prepared. each bath containing 8.6 percent of l,3-dimethylol-4.5-dihydroxy-Z- 7 imidazolidinone, 0.85 percent of zinc nitrate, and sodium actate or ethylenediaminetetraacetic acid, tetrasodium salt (EDTA) in the amounts shown in Table V. The pH of the pad baths containing EDTA were ad- The pad baths were applied by standard padding procedure to cotton broadcloth which had been prebrightened and preblued with an aqueous solution containing 0.5 percent of C. l. Fluorescent Brightening Agent 25, 0.03 percent of C. l. Vat Blue 6 and 0.25 percent of nonionic surface active agent.

The wet pickup was 70 percent. The fabrics, containing 6.0 percent on the weight of the fabric-of l.3dimethylol-4.5-dihydroxy-2-imidazolidinone, were dried for 1 minute at 225F.. steamed for 5 seconds and pressed for 5 seconds at 350F., and then heated in an oven for 8 minutes at 320F.

The wrinkle recovery of the fabrics was measured as described in Example 2. The laundering process is described in Example 1.

The tensile strength of the fabrics was measured by ASTM standard method using a Scott tensile strength tester.

The fabrics were inspected for discoloration by comparing the color of the treated fabrics with that of the untreated fabric.

. The results are shown in Table VI. Fabrics AF correspond to pad baths A-F, respectively.

TABLE VI The pad baths were applied by standard padding procedure to 65/35 polyester/cotton shirting prebrightened and preblued as described in Example 3, obtaining a wet pickup of 65 percent. The fabrics. containing 5.6 percent on the weight of the fabric of 1.3- dimethylol-4,5-dihydroxy-2-imidazolidinone, were dried for 1 minute at 225F., steamed 5 seconds and pressed for 5 seconds at 350F.. and then heated in an oven for 8 minutes at 320F.

The fabrics were inspected for discoloration and retention of creases after 5 launderings as described in Example 1.

The results are shown in Table Vlll. Fabrics A-F correspond to pad baths A-F, respectively.

Nine aqueous pad baths were prepared, each bath containing 8.6 percent of l,3-dimethylol-4,5-dihyq droxy-2-imidazolidinone. 0.85 percent of zinc nitrate,

0.25 percent of nonionic surface active agent, 0.5 percent of C. l. Fluorescent Brightening Agent 25, and sodium acetate or N.N-di)hydroxyethyl)glycine, sodium salt (DEG) as shown in Table IX. The pHs of the pad Wrinkle Recovery, W & F, Degrees Fabric Initial After 5 Washes Tensile Strength (Lb.) Discoloration A 292 276 59 Severe B 296 284 62 Slight C 289 299 59 Slight D 297 297 66 Very slight E 290 277 71 Very slight F 289 284 73 Very slight Untreated 2l4 I81 136 Very slight EXAMPLE 4 Six aqueous pad baths were prepared, each bath containing 8.6 percent of l.3-dimethylol-4.5-dihydroxy-2- imidazolidinone, 0.85 percent of zinc nitrate, and sodium acetate or ethylenediaminetetraacetic acid. tetrasodium salt (EDTA) in the amounts shown in Table VI]. The pHs of the pad baths containing EDTA shown in Table V were adjusted to 4.3 with hydrochloric acid.

baths as shown in Table IX represent unadjusted final bath pHs.

TABLE IX Pad Bath Additive None 0.07% 0.05% 0. NW1 0.2071 0.30% 0.40% 0.50% 0.60%

sodium acetate DEG DEG DEG DEG DEG DEG DEG TABLE X Discoloration Fabric Cotton Polyester/Cotton A Severe Severe 8 Severe Severe C Severe Severe D Moderate Severe E Slight Moderate F Very Slight Slight G Very Slight Very Slight H Very Slight Very Slight 1 Very Slight Very Slight EXAMPLE 6 Six aqueous pad baths were prepared, each bath con-i taining the amounts of l.3-dimethylol-4,5-dihydroxy-2- imidazolidinone and zinc nitrate shown in Table XI, 0.25 of a nonionic surface active agent, 0.5 percent of C. I. Fluorescent Brightening Agent 25, and the amount of sodium acetate or N,N-di(hydroxyethyl )glycine, sodium salt (DEG) shown in Table XI. The pH of the pad baths is also shown in Table XI.

TABLE XII Continued Imidazolidinone (on weight of Wrinkle Recovery W & F, Degrees 5 Fabric fabric) 320F. 360F. Discoloration D 5.5 233 273 Slight E 8.0 286 288 Severe F 8.0 279 270 Slight 0 EXAMPLE 7 Five aqueous pad baths were prepared, each bath containing 8.6 percent of l,3-dimethylol-4,5-dihydroxy2-imidazolidinone, 0.85 percent of zinc nitrate, 0.25 percent of a nonionic surface active agent, 0.5

the amount of sodium acetate or nitrilotriacetic acid (NTA) shown in Table XIII. The pI-Is of the pad baths containing NTA shown in Table XIII were adjusted to 4.7 with sodium hydroxide.

TABLE XIII percent of C. I. Fluorescent Brightening Agent and Pad Bath Additive 0.07% sodium acetate 0.271 NTA 0.05% NTA 0.02571 NTA The pad baths were applied to cotton broadcloth by standard padding procedure with a 70 percent wet pickup. The fabrics containing 6.0 percent on the weight of the fabrics of l,3-dimethylol-4,5-dihydroxy- 2-imidazolidinone were dried for one minute at 225F.

TABLE XI Pad Bath lmidazolidinone Zinc Nitrate pH Additive A 4.3% 0.4371 4.9 0.037% sodium acetate B 4.3% 0.43% 4.7 0.25% DEG C 7.9% 0.7971 4.8 0.068% sodium acetate D 7.9% 0.7971 4.7 0.46% DEG E l 1.5% L307 4.6 0.099% sodium acetate F ll.5% l.307r 4.7 0.6871 DEG The wrinkle recovery of the swatches heated for l minute at 320F. or 360F. was measured by the procedure of Example 2.

The swatches steamed, pressed and heated at 320F.

were inspected for discoloration by the procedure of Example I.

The results are shown in Table XII. Fabrics A-F correspond to pad baths A-F, respectively.

TABLE Xll Imidazolidinone Wrinkle Recovery 0? (on weight of W & F. Degrees Fabric fabric) 310F. 360l Discoloration A 'l3l 336 Slight B 217 130 Slight C 24} :60 Moderate Swatches of the dried fabric were l) heated at 320F. for 1 minute, (2) heated at 360F. for 1 minute, or (3) steamed for 5 seconds, pressed for 5 seconds at 350F., and then heated in an oven at 320F. for 8 minutes.

The wrinkle recovery of swatches heated for 1 minute at 320F. or 360F. were measured by the procedure of Example 2.

The swatches steamed, pressed and heated at 320F. were inspected for discoloring by the procedure of Example l.

The relative fluorescent intensity. a measurement of brightener activity, was measured by standard procedure using a fluorimeter.

The results are shown in Table XIV. Fabrics A-E correspond to pad baths A-E, respectively.

EXAMPLE 8 TABLE XV l5 Pad Bath Pad Pad Bath Stored Bath Additive Compatibility for l6 hours A 0.077! sodium acetate Very Cloudy No B 0.37: NTA Clear Yes C 0.271 NTA Clear Yes D 0.371 NTA Clear No E 0.27: NTA Clear No The pad baths were applied to cotton broadcloth by the procedure of Example 7. The wrinkle recovery, discoloration and fluorescent intensity were measured by the method of Example 7.

The results as shown in Table XVI. Fabrics A-E correspond to pad baths A-E, respectively.

TABLE XVI Wrinkle Recovery W 84 F. Degrees Fluorescent Fabric 320F. 360F. Discoloration Intensity '7:

A 275 272 Moderate 100 Y B 242 244 Very Slight I25 40 C 244 269 Slight 119 D 215 267 Very Slight I25 E 246 257 Slight I20 EXAMPLE 9 TABLE XVII Pad Bath EDTA A None B 0.38%

The pad baths were applied by standard padding procedure to 80 X 80 cotton percale dyed with 3.0 percent on the weight of the fabric of an indanthronc dye, C.

I. Vat Blue (C. I. No. 69825) obtaining a percent wet pick-up. The fabrics, containing 6.3 percent on the weight of the fabric of l,3-dimethylol-4,5-dihydroxy-2 imidazolidinone, were dried at 225F. for one minute, pressed for 15 seconds at 3 10F., and heated in an oven at 340F. for 10 minutes.

The fabrics were examined for shade change by comparing the treated fabrics with untreated dyed fabric.

The fabrics were laundered five times ina home-style washing machine using water at 120F. and tumble drying after each washing. The fabrics were then inspected for retention of creases placed in the fabric during the pressing operation.

The results are shown in Table XVIII. Fabrics A and B correspond to Pad Baths A and B, respectively.

TABLE XVIII Fabric Shade Change Crease Retention A Definite Excellent B Negligible Excellent EXAMPLE 10 TABLE XIX Pad Bath Citric Acid A None B 0.7%

The pH of the pad bath was adjusted to 4.7 by the addition of sodium hydroxide.

The pad baths were applied by standard padding procedure to X 80 cotton percale dyed with 3.0 percent on the weight of the fabric of an indanthrone dye, C. I. Vat Blue 6 (C. I. No. 69825), obtaining an 80 percent wet pick-up. The fabrics, containing 9.0 percent on the weight of the fabric of l,3-dimethylol-4,5-dihydroxy-2- imidazolidinone, were dried at 225F. for one minute, steamed for 5 seconds, pressed for 15 seconds at 310F., and heated in an oven at 380F. for 6 minutes.

The fabrics were examined for shade change by comparing the treated fabrics with untreated dyed fabric. The durable press properties of the two fabrics were also determined.

The results are shown in Table XX. Fabrics A and B correspond to Pad Baths A and B, respectively.

In the use of citric acid as the sequestering agent, sufficient sodium hydroxide is added to provide a pH of between about 4.5 and 5.5. Optimum pHs and levels of sequestering agent use will, of course, vary with the particualr source of resin, the textile to be treated and the finishing conditions to be employed. Optimization of such factors is well within the skill of the ordinary competent technician.

EXAMPLE 1 1 Three pad baths were prepared, each bath containing 1 1.3 percent of 1,3-dimethylol-4,5-dihydroxy-2- imidazolidinone, 1.25 percent of zinc nitrate, 0.25 per- .cent of a non-ionic surface active agent, 0.5 percent of TABLE XXI Pad Bath Citric Acid pH of Bath A None 4.5 B 0.7% 4.0 C 0.771 4.5

The pad baths were applied by standard padding procedure to white cotton broadcloth obtaining a 75 percent wet pick-up. The fabrics, containing 8.5 percent on the weight of the fabric of l,3-dimethylol-4,5-dihydroXy-2-imidazolidinone, were dried at 225F., steamed for 5 seconds, pressed for 5 seconds at 350F., and heated in an oven at 320F. for 8 minutes.

The wrinkle recovery of the fabrics was measured by the procedure of Example 2. The fabrics were inspected for discoloration by the procedure of Example 1.

The results are shown in Table XXII. Fabrics A, B and C correspond to Pad Baths, A. B and C, respectively.

The pad baths were applied by the procedure of Example 11 to white 65/35 polyester/cotton shirting obtaining 21 60 percent wet pick-up. The fabrics contained 6.75 percent of l,3-dimethylol-4.5-dihydroxy-2- imidazolidinone.

The fabrics were inspected for discoloration and appearance after 5 launderings as described in Example The results as shown in Table XXIII. Fabrics A, B

and C correspond to Pad Baths A, B anc C respectively.

TABLE XXIII Fabric Appearance Discoloration A Good Severe B Good Moderate C Good Slight While certain specific embodiments are preferred modes of practice have been set forth, this is solely for purposes of illustrating the invention, and it will be obvious that various changes and modifications may be made without departing from the spirit of the disclosure and the scope of the appended claims.

We claim:

1. A textile finishing composition useful for rendering cellulosic textile materials wrinkle resistant and providing permanent creases therein comprising an aqueous solution of 1,3-dimethylol-4,S-dihydroxy-Z- imidazolidinone, a zinc nitrate catalyst abd a sequestering agent; wherein the amount of the 1,3-dimethylol- 4,5-dihydroxy-2-imidazolidinone is sufficient to provide the textile to be treated with between 1.0 and 25.0 percent of said imidazolidinone based on the weight of said textile; the amount of zinc nitrate catalyst is between 5.5 and 16.5 percent based upon the weight of the imidazolidinone and the amount of sequestering agent is between 0.05 and 3.0 percent based on the weight of the solution.

2. A composition according to claim 1 wherein the amount of the imidazolidinone is between 3.0 and 8.0 percent, based on the weight of the textile.

3. A composition according to claim 1 wherein the amount of the catalyst is between 9.5 and 12.5 percent, based on the weight of the imidazolidinone.

4. A composition according to claim 1 wherein the amount of the sequestering agent is between 0.15 and 1.0 percent, based on the weight of the solution.

5. A composition according to claim 1 wherein the amounts of the imidazolidinone, zinc nitrate catalyst and sequestering agent are between 3.0 and 8.0 percent based on the weight of the textile; 9.5 and 12.5 percent based on the weight of imidazolidinone; and between 0.15 and 1.0 percent based on the weight of the solution, respectively.

6. A composition according to claim 1 wherein the sequestering agent in said composition is a partially neutralized alkali metal salt of an amino polycarboxylic acid or of an hydroxy carboxylic acid.

7. A composition according to claim 6 wherein said acids are selected from the group consisting of ethylenediaminetetraacetic acid, nitrilotriacetic acid, di( hydroxyethyl )glycine, (hydroxyethyl )ethylenediaminetriacetic acid, diethylenetriaminepentaacetic acid, gluconic acid, citric acid, and tartaric acid.

8. A composition according to claim 1 wherein the sequestering agent is a partially neutralized sodium salt of citric acid.

9. A composition according to claim 1 wherein the sequestering agent is a partially neutralized sodium salt of malic acid.

10. A composition according to claim 5 wherein the sequestering agent is a partially neutralized sodium salt of citric acid.

11. A composition according to claim 5 wherein the sequestering agent is a partially neutralized sodium salt 

1. A TEXTILE FINISHING COMPOSITION USEFUL FOR RENDERING CELLULOSIC TEXTILE MATERIALS WRINKLE RESISTANT AND PROVIDING PERMANENT CREASES THEREIN COMPRISING AN AQUEOUS SOLUTION OF 1,3DIMETHYLOL-F,5-DIHYDROXY-2-IMIDAZOLIDINONE, A ZINC NITRATE CATALYST ABD A SEQUESTERING AGENT, WHEREIN THE AMOUNT OF THE 1,3-DIMETHYLOL-4,5-DIHYDROXY-2IMIDAZOLIDINONE IS SUFFICIENT TO PROVIDE THE TETILE TO BE TRRATED WITH BETWEEN 1.0 AND 25.0 PERCENT OF SAID IMIDAZOLIDINONE BASED ON THE WEIGHT OF SAID TEXTILE, THE AMOUNT OF ZINC NITRATE CATALYST IS BETWEEN 5.5 AND 16.5 PERCENT BASED UPON THE WEIGHT OF THE IMIDZOLIDINONE AND THE AMOUNT OF SEQUENTERING AGENT IS BETWEEN 0.05 AND 3.0 PERCENT BASED ON THE WEIGHT OF THE SOLUTION.
 2. A composition according to claim 1 wherein the amount of the imidazolidinone is between 3.0 and 8.0 percent, based on thE weight of the textile.
 3. A composition according to claim 1 wherein the amount of the catalyst is between 9.5 and 12.5 percent, based on the weight of the imidazolidinone.
 4. A composition according to claim 1 wherein the amount of the sequestering agent is between 0.15 and 1.0 percent, based on the weight of the solution.
 5. A composition according to claim 1 wherein the amounts of the imidazolidinone, zinc nitrate catalyst and sequestering agent are between 3.0 and 8.0 percent based on the weight of the textile; 9.5 and 12.5 percent based on the weight of imidazolidinone; and between 0.15 and 1.0 percent based on the weight of the solution, respectively.
 6. A composition according to claim 1 wherein the sequestering agent in said composition is a partially neutralized alkali metal salt of an amino polycarboxylic acid or of an hydroxy carboxylic acid.
 7. A composition according to claim 6 wherein said acids are selected from the group consisting of ethylenediaminetetraacetic acid, nitrilotriacetic acid, di(hydroxyethyl)glycine, (hydroxyethyl)ethylenediaminetriacetic acid, diethylenetriaminepentaacetic acid, gluconic acid, citric acid, and tartaric acid.
 8. A composition according to claim 1 wherein the sequestering agent is a partially neutralized sodium salt of citric acid.
 9. A composition according to claim 1 wherein the sequestering agent is a partially neutralized sodium salt of malic acid.
 10. A composition according to claim 5 wherein the sequestering agent is a partially neutralized sodium salt of citric acid.
 11. A composition according to claim 5 wherein the sequestering agent is a partially neutralized sodium salt of malic acid. 